Bookmarked by Reese’s Book Club

Episode: From Startup Queen to Novelist: Why Ali Kriegsman Self-Published
Date: September 16, 2025
Host: Danielle Robay
Guest: Ali Kriegsman

Overview

This episode explores the fearless transformation of Ali Kriegsman from successful tech entrepreneur and celebrated business author to debut novelist—one who has charted her own course through the world of self-publishing. Host Danielle Robay dives deep into Ali’s decision to upend her career and personal life, the tough crossroads she navigated, and the creative, hands-on campaign she designed to bring her satirical thriller "The Raise" to readers. Their conversation offers inspiration and practical advice for anyone standing at a crossroads, dreaming of betting on themselves, and for writers daunted by traditional gatekeepers.

Key Discussion Points & Insights

Ali’s Radical Life and Career Shift

• Ali recounts her journey from working at Conde Nast and founding the startup Bulletin to selling the company for eight figures and feeling unfulfilled despite impressive accolades such as Forbes 30 Under 30.
• After joining another startup and discovering ethical issues, she decided to walk away, realizing that her self-worth had been too entwined with external validation (08:06 – 10:04).
• Quote:
  “I collected all the titles ... using their validation as a shorthand for my internal validation. It wasn’t working for me anymore ... I have to find some other journey to self belief and self publishing the raise is what got me there.”
  — Ali Kriegsman (10:04)

Choosing Self-Publishing Over Traditional Paths

• After initial rejections from traditional publishers (who didn’t know how to market "startup fiction"), Ali decided to self-publish, regaining creative and logistical control—and investing financially and emotionally in her own vision (08:06 – 11:41; 14:21).
• She describes using her skills as a marketer and entrepreneur to craft a unique book launch: directing every aspect from the cover to the marketing, PR, and even producing a cinematic book trailer.
• Quote:
  “Going the self publishing route … and publishing the book myself … and all of this upfront spending, like, terrorized me at night. But … I had to stomach [it] with the hope that ultimately it would pay off.”
  — Ali Kriegsman (14:21)

Identity, Reinvention, and Internal Validation

• Ali discusses the process of ‘burning down’ her former life to pursue genuine self-worth:
  “In order to become the person you want to be ... it really demands a fundamental mindset shift and almost like a complete overhaul of your internal software.”
  — Ali Kriegsman (15:37)
• She enumerates the questions she asked herself during her reinvention, such as:
  • What do I want to be known for?
  • What unfulfilled desires exist?
  • What signals do I want to send the universe?
    (12:23–13:57)
• Host Danielle emphasizes the power of thoughtfully asking yourself the right questions (11:41–12:23).

The Mechanics of Self-Publishing

• Ali admits her initial ignorance (“I literally started looking for a physical book binder in New York”) and encourages listeners that being a novice is not a barrier (23:06).
• She details how she found partners, built a team, and prioritized working with specific creative women—or not doing it at all if they weren’t available (23:56).
• The unique freedom in self-publishing: Ali handpicked everything, from launch date to creative direction, marketing strategy, and more—contrasting with the many limits of traditional publishing. (25:51)

Marketing The Raise: A Startup Mindset

• Ali brings a startup’s branding sophistication—dedicated website, professional actors playing characters, cinematic trailers, postcards, brand colors, custom soundtracks—to the book’s campaign (25:51 – 28:46).

• On integrating visual media and digital strategies:

  “Books are not just competing with other books anymore. They are competing with all forms of media … The raise is not going to be this one dimensional book. It's going to be a universe.“
  — Ali Kriegsman (25:51)

• The viral TikTok/Instagram campaign was partly improvised: actors filmed POV content during the trailer shoot, happening because of necessity and Ali’s willingness to pivot on the fly (29:18–30:53).

Lessons Learned and Advice for Creatives

• Ali’s #1 takeaway: don’t let industry rejections define you.
  “It is so easy to let other people's opinions or rejection of you become a part of your identity. … if you have that spidey sense inside … you have to listen to it.”
  — Ali Kriegsman (31:03)
• Host Danielle and Ali discuss trusting your gut over external gatekeepers, with reference to Lady Gaga’s journey (31:03).
• On creating lasting change: “Chip away at your dream a little bit every day ... Give yourself grace and give yourself the breathing room to chip away at it little by little, because that’s how it’s going to get done.” (51:04)

Book Discussion: The Raise

Structure and Genre

• "The Raise" is a satirical psychological thriller, blending humor, suspense, startup satire, and themes of codependency and self-discovery.
  “This is a very vulnerable piece ... every character is fiction, but there are very deep emotional truths in this book.”
  — Ali Kriegsman (40:02)
• Ali’s goal: write a gripping book readers are “addicted to” and finish in 24–48 hours (37:53).
• The story and characters draw on her real startup experiences, with the protagonist’s journey toward internal validation reflecting her own (42:13).

Creative Process

• The opening scene—buying a wig for her cofounder’s corpse—came to her on a flight and was written, ferociously, in the moment (38:53).
• She wrote sequentially and iteratively, with five years from inception to publication (39:51).

Intended Audience & Themes

• Written especially “for women in their 20s” who are ambitious, uncertain, and seeking meaning and validation—but accessible and engaging for anyone (42:13).
• Touches on universal themes:
  • How well do you know those closest to you?
  • The danger of clinging to what you “know for sure” (Mark Twain quote, 44:10).
• The immersive yet accessible startup world has validated readers, especially women in tech, who feel “seen” by Ali’s authentic depiction (46:19).

Notable Quotes & Moments

• “Your new life is going to cost you your old one.”
  — Repeated, reframed, and explored as both a cliché and a profound truth (15:11)

• “I decided that ... as a way of life, it can't be how I operate anymore. I have to find a new way of feeling internally valid.”
  — Ali Kriegsman (10:04)

• On branding the book as if it were a startup:
  “I gave it a dedicated website, cast actors ... did a whole photo shoot ... I decided that for this cinematic trailer, this movie trailer, that I was going to pull you into the world of the raise.”
  — Ali Kriegsman (25:51)

• “Nature desires a trade. Your courage in exchange for your dream.”
  — Ali’s “woo woo” Instagram quote of the week (47:15)

Key Timestamps

• 03:13–04:54: Introduction to Ali Kriegsman’s career journey
• 06:01–07:27: The wild opening scene of "The Raise"
• 08:06–11:41: Ali’s career U-turn, failed traditional publishing attempt, pivot to self-publishing
• 12:23–14:56: Internal questions guiding Ali’s reinvention
• 15:11–17:41: “Your new life is going to cost you your old one”—deconstructing the saying
• 22:00–25:05: Self-publishing process, building a creative team
• 25:51–29:18: Ali’s marketing strategy, the “startup” approach
• 29:18–30:53: TikTok/Instagram social content improvisation
• 31:03–32:55: Lessons on outside rejection and self-trust
• 37:04–41:02: "The Raise"—Genre, process, emotional truths
• 42:13–44:10: Who the book is really for
• 45:43–46:55: Reader reactions and community response
• 47:09: Inspirational quote—nature, dreams, and courage
• 47:57–49:24: Book recommendations for creative transformation
• 51:04: Ali’s top advice: chip away at your dream daily
• 53:22–54:49: Speed round: Ali’s rapid-fire book and literary answers

Book & Resource Recommendations

• For internal transformation:

  • The Untethered Soul by Michael A. Singer
  • The Artist’s Way by Julia Cameron
  • Designing Your Life by Bill Burnett & Dave Evans

• For inspiration or genre fans:

  • Yellowface by R.F. Kuang
  • Luckiest Girl Alive by Jessica Knoll
  • My Brilliant Friend by Elena Ferrante
  • No One Is Talking About This by Patricia Lockwood

Final Takeaways

• Redefining success often means letting go of institutional validation and building self-worth from within.
• Self-publishing, far from being a consolation, can be a form of creative and professional liberation—provided you’re willing to put in the work.
• The hustle of launching a book can be as creative and entrepreneurial as starting a company.
• The most transformative and resonant stories are those rooted in emotional truth, especially for readers seeking to see themselves reflected with honesty and empathy.
• “Chip away at your dream a little bit every day ... That’s how it’s going to get done. And that’s how you’re going to build the confidence up necessary to do the full version of it.” — Ali Kriegsman (51:04)

For artists, entrepreneurs, and aspiring writers: this episode is both inspiring and a toolkit for mapping your own journey beyond the mainstream.